Potassium Iodide → HCID 10588819, compound

HRID 636251Notes

Reaction equation

HRID 636251 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:13][C:14]1C=C(C)C=CC=1S([O-])(=O)=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-]#[N:32].[K+].C1OCCOCCOCCOCCOCCOC1.[I-].[K+]>CN(C)C=O>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:13][C:14]#[N:32])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 131722399HCID 131722399, compound

Product 1

HCID 10588819HCID 10588819, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

60.5 g of ((R)-2-benzyloxycarbonylamino-2-phenylethyl)-4-methylphenylsulphonate (142.2 mmol) are dissolved in 675 ml of dimethylformamide. 13.9 g of potassium cyanide (213.3 mmol), 5.64 g of 18-crown-6 (21.33 mmol) and 520 mg of potassium iodide (3.13 mmol) are added and the mixture is stirred at 50° C. for 20 hours. The reaction solution is poured into 500 ml of ice water and this mixture is subsequently stirred at 0° C. for 5 hours. The mixture is filtered with suction and the precipitate is dissolved in ethyl acetate. The organic phase is washed three times with water, dried over magnesium sulphate and concentrated in vacuo. The residue is triturated with diethyl ether, filtered off with suction, washed with diethyl ether and dried over phosphorus pentoxide.

Workup

  1. stirringthis mixture is subsequently stirred at 0° C. for 5 hours
  2. filtrationThe mixture is filtered with suction
  3. dissolutionthe precipitate is dissolved in ethyl acetate
  4. washThe organic phase is washed three times with water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe residue is triturated with diethyl ether
  8. filtrationfiltered off with suction
  9. washwashed with diethyl ether
  10. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-0458b6b288a94b37a4032e908d053396
Source dataset
uspto-grants-2001_02
Patent number
US06191282B1

Reaction notes

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